Photographic developers containing acylamino groups



- graphic images.

Patented May 30, 1944 PHOTOGRAPHIO DEVELOPERS CONTAINING ACYLAM INO GROUPS Wesley T. Hanson, Jr., Roehester, N. Y., assignmto Eastman Kodak Company,

Rochester, N. Y.,

a corporation of NewJersey No Drawing. Application September 11, 1941, Serial No. 410,422

8 Claims. (01. 95-88) This invention relates to photographic'developers and more particularly to p-phenylenediamine developers containing acylaminogroups.

It is known that photographic developers of 'the p-phenylenediamine type are valuable com-, pounds for producing fine grain black and white photographic images and also that these compounds, especially when they contain alkyl substituents on one of the nitrogen atoms, are useful as developers in producing colored photo- A serious disadvantage of the p-phenylenediamine developers is that they are highly allergenic, that is, are poisonous to the human skin and, therefore, are somewhat dangerous to use. When the p-phenylenedia'mines are used in color development processes, it has also been found that they do not always produce the desired color in the final image.

It is, therefore, the principal object of the present invention to provide a new class of photographic developing agents of the p-phenylenediamine type. A further object is to provide photographic developing agents which are less allergenic, that is, less poisonous to the human skin, than the p-phenylenediamines. A still further object is to provide photographic developing agents of the substituted p-phenylenediamine type which are useful in photographic color processes for the purpose of producing images of the desired color.

These objects are accomplished by the present invention by the use as developing agents of acylamino-4-aminodialky1-anilines.

Compounds suitable for use in my invention are dialkyl-p-phenylenediamines having acylamino substituents such as acetylamino or propionylamino groups on the ring. Dialkyl-pphenylenediamines such as dimethyl-p-phenylenediamine and diethyl-p-phenylenediamine are suitablefor introduction of the acylamino group. One of the specific compounds which I have found suitable for use'according to our invention is 3-acetylamino-4-aminodimethylaniline. This compound is prepared by reducing m-nitrodimethylaniline to the amine and acetylating it with acetic anhydride and glacial acetic acid.

The acetylaminodimethylaniline is nitrosated by treatment with sodium nitrite in 2-N-hydrochloric 'acid and the nitroso derivative reduced at room temperature with hydrogen by using a Raney nickel catalyst.

The compounds which I propose to use may be further substituted in the aromatic ring with other groups including halide, amino, substituted amino, azo, alkyl and aryl groups. These groups Peterson U. S. Patents tend to alter the color of the color of way.

When used for the formation of colored photographic images, the developers of my invention may be used in conjunction with any well known coupler compounds such as those described in Fischer U. S. Patent 1,102,028, granted June 30, 1914; Mannes 8r Godowsky U. S. Patent 2,108,602. granted February 15, 1938; Mannes, Godowsky 8: 2,115,394, granted April 26, 1938 and 2,126,337, granted August 9, 1938.

The following example illustrates a developing solution which may be used according to my inthe lmage may be controlled in this vention:

A. 3-acetylamino-4-aminodimethylaniline g ams 2 Sodium sulfite do 1 Sodium carbonate -do 30 Water to n." 1

B. Coupler ...gram.. 1 Acetone PP 50 B is added to A The developing agents described in the present application may be used to form photographic images by development of exposed silver halide contained inthe usual gelatin carrier or rip carriers such as collodion, water-permeable cellulose esters or water-permeable synthetic resins. The sensitive layers may be carried on any suitable support such as glass, paper, cellulose ester or synthetic resins. They may be used with multi-layer films where two or more layers are coated on the same side ofa support or where the layers are coated on the opposite sides of a support.

It will He understood that the examples included herein are illustrative only and that my invention is to be taken as limited only by the scope of the appended claims.

I claim:

1. A photographic developing solution comprising as the developing agent a lower fatty acid acylamino-4-aminodialkylaniline.

2. A photographic developing solution comprising as the developing agent a 4-aminodialkylaniline having a lower fatty acid acylamino group in the 3-position. v

3. A photographic developing solution comprising as the developing agent a 3-acetylamino- 4-aminodialkylaniline.

4. A photographic developing solution compristhe final dye image and ing as the developing agent 3-acetylemino-4- aminodimethylaniline. i

5. A photographic developing solution for producing a, colored image comprising a lower fatty acid acylamino-4-aminodialkylaniline as the developing agent and a. compound which couples with the developing agent on photographic development to form a. colored image.

6. A photographic developing solution for producing a colored image comprising 3-aqetvlamino-4-aminodimethylaniline as the developing agent and a compound which couples with the developing agent on photographic development to form a colored image.

7. The method of producing a colored photonewton graphic e in e geletino silver lide emulsion layer which comprises coupling the development product of a. lower fatty cold ncyl 4-eminodialkyleniline developing agent with a compound which couples with the developing agent on development.

8. The method of producing a, colored photo graphic image in e geletino silver halide emul= sion layer which comprises coup n the devel-= opment product of 3-9icety1nO-4?|l|i.h methylaniline with a. compound which couples with the 3-ecetylamino-4-aminethyline on development.

WES .iil' T. the; JR. 

